The album opens with the title track, High Wide and Handsome, which finds Wainwright the song writer taking on the persona of Poole to celebrate his high living and hard drinking style. The song is as balls out as anything on a new OCMS album and it is what we would expect from Wainwright. Yet a mere two tracks later he has settled into the sweet, almost cheesy lyrics of Poole’s My Mother and My Sweetheart. This is where the album really gets special—in a post-modern era where Irony is king and Wainwright one of its very loyal subject, seeing him indulging in and embracing the sort of treachy sentimentalism which went out of fashion before Woodstock is a breath of fresh air. Wainwright even tries his has at this brand of sentimentalism with Rowena, a song based on the letters his grandfather wrote to his grandmother.
The album itself it not exactly a modernization, but neither does it suffer from the sort of copy cat syndrome that drags down so many other cover albums. For starters, Loudon’s dry and dusty vocals do not allow themselves to be used in the same manner as Charlie’s more liquid ones. There is what feels like an intentional effort to stay with the instrumentation and style of the period, but that serves to highlight the songs rather than distract from Wainwright’s performances. To borrow a phrase from Top Chef, High Wide and Handsome uses Poole’s music as an inspiration rather than seeking to create a literal translation.